Black azo dyestuffs and process of making same



Patented Apr, l7, 1%23.

users r rarest nuance.

AUGUST LEOPOLID LASKA AND ARTHUR ZITSCHIEE, F OFFENBACH-ON-THE-MMN, GERMANY, ASSIGNORS T0 CHEMIfiCHE FAEBIK GRIESHEIM-ELEKTRQN, 0F FRABTKFQRT-ON-THE-MAIN, GERMANY, A CORPORATION.

BLACK A DYESTUFFS AND PROCESS (OF MAKIENG SAME.

36o Entering.

The new dyestufi's, having probably the general formula Aryl-N=N X..

Wot I wherein X means the residue of an l-naphthylamin compound capable of combining in the 4-position and not containing a sulfo group, R an aromatic radical, are when dry black powders, with metallic lustre, insoluble in water and soluble in concentrated sulfuric acid to a blue to green solution, yielding upon reduction with stannous chlorid an arylarnin, an lA-diamino-compound of the napththalene series and an arylid of l-ainino-2-oxy-3-naphthoic acid, and dyeing, when produced on the fiber, cotton in black shades of an excellent fastness.

As diazocomponents can be used all the arm ino-azo-compounds, which are obtained by combining diazotized aromatic amins, such as anilin, its homologues and substitution to products such as toluidines, xylidines, anisidines, phenetidines, cresidines, thio-anisidines and their negatively substituted derivatives such as chloro-derivatives, monoacylphenylen-diamines, and aminoquinolines, naphth lamins and so on with l-naphthylamin or its derivatives capable of combining in l-position and not containing a sulfo group, such as l-aminonaphtholalkylether, l-aminomethylnaphthalene and so on. As azo components all the arylamids of 2.3-oxynaphthoic acid can be used, such as the anilid, toluidides, anisidids and phenotidids, czand -napthalid, nitroanilids, di-m-toluylene and p-phenylendiamin comso pounds, whereby two molecules of the diazo Application filed August 9, 1922.

serial No. 530,?59.

compound react, arylids chloro-substituted in the arylid residue and so on.

According to the component used reddish, bluish or greenish darkly black shades are obtained.

The fastness to light of the colored fabrics can be increased by an after treatment with copper salts.

The following examples illustrate the invention, the parts being by Weight.

EXAMPLE 1.

30.5 parts of o-ethoxy-m-toluene-azo-lnaphthylamin are dissolved in 1-0 parts of hydrochloric acid 20 B. and about 4500 parts of Water and diazotized in the usual manner with 6.0 parts of sodium nitrite. The diazo compound so formed, is separated by filtration from a small quantity of impurities. 29.3 parts of p-anisidid or" 2.3-oxynaphthoic acid are dissolved in 20 parts of caustic soda lye 36 B6. and 200 parts of warm water after addition of an aqueous solution of 13 parts of sodium acetate and 2 parts of Turkey red oil, cooled with ice to @Q, about 10 C. and filtered.

This solution is poured while stirring into the diazo-solution at 1015 C. When the combination is complete the dyestufl, thus formed is filtered, Washed and dried. lit forms a bluish black powder with metallic lustre, soluble in concentrated sulfuric acid to a green solution and precipitatable by water in bluish black flakes.

EXAMPLE 2. Dyeing yam.

PADDING-BATH.

DYE-BATH.

50 gr. of benzene-azo-l-naphthylamin or 56 gr. of o-anisol-azo-l-naphthylamin' are diazotized after addition of 60 cc. of hydrochloric acid 20 B. and 3000 cc. of cold water by means of a solution of 15 gr. of

nitrite of soda in 100 cc. of water. The whole is made u to 10 litres.

Before using t e free mineral acid is neutralized with acetate of soda. The padded yarn is handled for some time in the dye bath, washed, soaped and finished.

EXAMPLE 3. Dyeing piece-goods.

PADDING-BATH.

120 gr. of a-naphthalid or 80 gr. of naphthalid of 2.3-oXyna-phthoic acid are dissolved with 200 cc. of caustic soda lye 34 B. and 250 cc. of Turkey red oil in the quantity of water, .Which is necessary at 30-40 C. to 10 litres.

The piece is padded with the solution, strictly pressed or dried and introduced in the following dye-bath.

DYE-BATH.

73 gr. of p-toluene-azo-l-amino-2-naphthol-methylether are diazotized after addition of 75 cc. hydrochloric acid 20 B. and the quantity of water, which is necessary, by

means of a solution of 18.? gr" nitrate of' soda in 100 cc. of water and made up to 10 litres.

Before using the free mineral acid is neutralized with acetate of soda.

The following table gives some of the shades obtained according to this invention:

Combined with Diazo compound of the the arylid of Shade amino-azo compound from 2.3-oxynahthoic Anl1in+l-naphthy1amin Anilid(example 2). Reddish black. O-anisidin+ .do .do Vi0letblack. P-anisidin+ .do. Bluish black. M-anisidin+ ..do. Violet-black. P-phenetidin+ .do D P-xylidin+ .do Bluish black. P-cresidin+ do Du O-anisidin+ .do Black. P-cresidin+ .do Bluish black. P-eresidin+1-amino-2 meth- .do Violet-black.

yhiaphthali'n. P-tolu1din+l-amino-Z-naph- .do.(examp1e 3) Bhnsh black.

tholmcthylether. P-cresidiu+l amino-2-naph- .do Grecnish black.

tholmethylether. P-anisidin+1amino-2-naph- .do Do.

tholethylether. O-anisidin+1-naphthylamin a-naphthahd (ex- Violet-black.

811211316 2). P-toluidin+ .do o Reddish black. P-cresidin+ .do Violet-black. O-aminoquinoline+.do D P-cresidin+l-amino-i rmethyl- D naphthalene. O-chloranilin+l-amino-2- Greemsh black.

naphtholmethylether. M-chloranilin+1-amino-2- Do.

na. htholmethylether. P-c oraujlin+1-smino-2- Black. na htholmethylether. P-to uidin+1-amino-2-naph- .do.(example 3) Bluish black.

tholmethylether. O-anis'idin +1-amino-2-naph- .do Black.

tholmethylether. 4-Ch1oro-1.2anisidine+1-ami- .do Greenish black.

no-Z-naghtholmethyhther. i-Aminot ioanisoI-i-l-amlno- .do Do.

2-naphtholmethylethen O-phenetidin+1-amino-2- .do Greenish black.

naphtholethylether.

dyestuffs have probably the general formula RHNOC wherein X means the residue of an 4-naphthylamin compound capable of combining in the le-position and-not containing a sulfo group, R an aromatic radical, which dyestuffs are when dry, black powders with metallic lustre, insoluble in water and soluble in concentrated sulfuric acid to a blue to green solution, yielding upon reduction with stannous chlorid an arylamin, a lA-diamino compound of the naphthalene series and an arylid of l-amino-2-oxy-3-naphthoic acid, and, when produced on the fiber, dyeing cotton in black shades of an excellent fastness.

9.. Textile material dyed With the new azodyestuff as covered in claim 1, said dyestuff being developed on the material.

3. As new articles the azo dyestuffs, which can be obtained by combining an alkoxyphenyl-azo-l-naphthylamin compound not containing a sulfo group with an arylamid of 2.3-oxynaphthoic acid, which dyestuffs have probably the general formula wherein X means the residue of an l-naphthylamin compound capable of combining in 4-position and not containing a sulfo group, R an aromatic radical, which dyestuffs are when dry black powders with metallic lustre, insoluble in water and soluble in concentrated sulfuric acid to a blue to green solution, yielding upon reduction with stannous chlorid an alkoxy-anilin, a 1.4 diaminocompound of the naphthalene series and an arylid of lamino-2-oxy-3-naphthoic acid, and, when produced on the fiber, dyeing cotton in black shades of an excellent fastness.

4. Textile material dyed with the new azodyestufi' as covered in claim 3, said dyestufi being developed on the material.

5. As new articles the azo dyestuffs, which can be obtained by combining the diazo com- RHNOC pound of an alkoxy-phenyl-azo-Q-alkoxy-lna hthoic acid which dyestufis have probnaphthylamin with an arylamid of 2.3-oxyab y the general formula:

0-Alkyl wherein R means an aromatic radical, which dyestufis are when dry black powders with metallic lustre, insoluble in water and soluble in concentrated sulfuric acid to a blue to green solution, yieldingiipon reduction with stannous chlorid an alkoxy-anilin, a 2-alkoxy lA-diaminonaphthalene and an arylid of 1- amino-2-oxy-3-naphthoic acid,and when produced on the fiber, dyeing cotton in black shades of an excellent fastness.

H gig N=N RHNOC 6. Textile material dyed with the new azodyestufi as covered in claim 5, said dyestufi being developed on the material.

7. As new articles the azo dyestuffs, which can be obtained by combining the diazo compound of an alkoxy-phenyl-azo-2-alkoxy-1- naphthylamin with a naphthalid of 2.3-oxynaphthoic acid, which dyestufis have probwhich dyestulfs are when dry black powders with metallic lustre, insoluble in water and soluble in concentrated sulfuric acid to a blue to green solution, yielding upon reduction with stannous chlorid an alkoxy-anilin, a 2- alkoxy-1.4-diaminonaphthalene and a naphthalid of 1-amino-2-oxy-3-naphthoic acid, and, when producedon the fiber, dyeing cotton in black shades of an excellent fastness.

8. Textile material dyed with the new azoably the general formula m hm l-nmock W AUGUST LEOPOLD LASKA. ARTHUR ZITSCHER Witnesses:

PETER LAUTENSCHLAGER, FRIEDRICH Dnson. 

